Season 5: ‘Insecure’ continues to tackle Hollywood’s challenges

Written by Staff Writer at CNN It’s been more than a year since “Insecure” ended its second season — but the mood on the set of its new season didn’t drastically change in that…

Season 5: 'Insecure' continues to tackle Hollywood's challenges

Written by Staff Writer at CNN

It’s been more than a year since “Insecure” ended its second season — but the mood on the set of its new season didn’t drastically change in that time.

While there have been snags in the cast’s relationships with their significant others, the dynamic between the friends remained as strong as ever, according to show creator and executive producer Issa Rae.

“There were some pieces that were off with parts of our work,” she told reporters Tuesday afternoon at a screening for season five, ahead of its release December 5. “Things that we did, we worked super hard on, but for the most part, our show just stayed really fast and feel good.”

“The conversation continues to shift, we’ve still got to fight and we’re still figuring out ways to do it,” she added. “We’re still figuring out who we are and what we want.”

As is typical with HBO comedies, the five-episode fifth season is structured as an episode and then an episode-long stand-alone stand-alone episode, built around a theme from each episode and introduced each lead character to the audience in a different way. (Laying the groundwork for seasons 6 and 7, Season 5 is the final season of the show.)

The unassuming (mostly)

Issa Rae in “Insecure” Season 5. Credit: HBO

HBO has been playing a game with “Insecure” fans lately, leading with the season five premiere of its latest season, only to released the season entirely later than usual — harkening back to the pilot of “Insecure,” which didn’t hit the air until three years after the show’s first season.

A press day in Los Angeles for season five on Tuesday began with five hour-long episodes (plus two shorts), lasting a total of 14 hours — a lengthy process for HBO’s binge-friendly brand, and a first for “Insecure.”

“Insecure” second season, Season 3. Credit: HBO

Season 5 has drawn big crowds at the screening, but the hype that’s already built around the drama set in Hollywood, a city that is as political as it is sexual, is a familiar one.

“I know there’s been so much hullabaloo about this show so many years in the making,” Rae said. “It’s hard for us to listen and say, ‘Oh man, yeah we’re trying to stay in your lap.’ But sometimes, you have to do that because that’s what is possible with something as unique as ‘Insecure.'”

“Hopefully, it’s making a dent in the world. I know that saying is rare, but sometimes it’s a thing that people think they know about a show and they don’t necessarily catch it until after we drop it on the world.”

Episode 1 to 5 from “Insecure” Season 5. Credit: HBO

A year’s progress

By the time Season 5’s red carpet premiere rolled around, Rae had seen a significant difference in her creative process. When the show was first conceived, the thinking was that Rae wouldn’t take breaks. Instead, she was inspired to create a series in the way that she was working — with her hands.

She wanted to create characters who were honest, truthful and relatable to herself and fans of “Insecure,” and she took that consideration when crafting the character of Joy.

“I just realized all of a sudden, I was so used to writing as myself,” she said. “So now I just try to expand and do stuff that allows me to channel myself. I’m finding more and more exciting ways to express myself, which is really freeing.”

The cast opening door to Season 5, Season 5. Credit: HBO

Rae plans to release short films from “Insecure” throughout the rest of her filmmaking career, as part of a project she’s working on with her daughter, Indya Moore, and friend and fellow “Insecure” star Yvonne Orji.

For her, the joy of writing is coming from creating something she doesn’t see coming, not assuming that the world will accept the perception she has created.

“I can’t wait to show people the movie, I can’t wait to see people’s reactions, I can’t wait to see them thinking the entire thing was true,” she said. “Because that’s all I’m hoping for.”

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